What Could Have Been
by MyMind'sDream
Summary: A series of one-shots. Sam had already lost his mother, and the love of his life, what more could he possibly learn that could hurt him. What will happen when he finds out a secret that Jess was hiding and how will it change his future?
1. 1: Hidden Truths

**A/N:** Hey! This random idea came to me and I just had to write it down! I think it'll work best in a series of one shots so here goes nothing. Hope you enjoy!

**Disclaimer: **I don't own Supernatural :/

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It had been a month since Jess's death. After many, many calls from his landlord Sam realized he had to go back to clean out his apartment. He had been dreading this moment for weeks.

After Jess's death, Sam threw some things in a duffle and went back on the road with Dean. He had to find that demon. He HAD to avenge Jessica's death. It was all he could think about. First his mother, now Jess.

When Sam decided to skip that interview, he was turning his back on his life in California. He knew when got to that town, he would start seeing Jess everywhere. He knew when he went to pack up what was left of their things; those memories would come rushing back. He was also certain, that the moment he stepped in that door, he would see her burning on the ceiling over their bed.

Sam jolted awake, sweating and panting, in the passenger seat of the Impala. Dean's gruff voice called out and he slapped his little brother on the shoulder, looking away from the road momentarily. This happened almost every time Sam fell asleep now.

"Hey! Hey! Sam! It's just a nightmare. We are ten minutes out of Stanford."

Trying to catch his breath, Sam nodded. He leaned his head down and caught his face in his hands, elbow rested on the car door. Concern colored Dean's features.

"Sammy, you sure you can do this? I can drop you off and go take care of it, if you changed your mind."

"Nah, man. I have to do this. I owe it to Jess. Plus, I need to talk to my landlord, apologize for bailing like that."

"I'm sure he would understand if you sent me. Listen man, if you change your mind just let me know."

Sam just tilted his chin up in acknowledgment. Taking slow even breaths, he attempted to calm himself. Ten minutes, that's all he had. In ten minutes he would be facing his worst nightmares, literally.

Three AC/DC songs later, the Impala rolled past the 'Welcome to Stanford' sign. The town looked just as he had left it…he was the one who changed. As they cruised through town he tried not to see the bar he and Jess had frequented, the track where they used to run, the bookstore/coffee shop they spent hours a week in or the food joint they shared their first kiss outside of.

THIS was true torture. All those memories, gone, just like that. All that time spent for what…nothing but pain. Every ounce of his heart…wasted. He should have known better than to get so close to someone. When had he ever had anything good in his life last?

Heating up, he started to feel a little dizzy. Leaning his head back as far as possible, Sam tried to block out the memories. If he couldn't handle this, there was no way he would survive their apartment.

Feeling the car jar to a halt, Sam looked ahead of him. They had arrived. He felt Dean's hand brace his shoulder and grip tight to get his attention.

"We can turn back now, Sammy. I promise, you don't have to do this."

"Yes, I do, Dean."

His voice came out a lot more hoarse than he thought it would. Opening the door, he turned and climbed out, slamming it shut behind him. He started the trek to Jess and his place. Dean followed close behind, a bunch of flat boxes in his arms.

At the door, keys in hand, Sam's anxiety was obvious. Those typically steady hands had a noticeable tremor as he attempted to pick the right key on his key ring. Dropping them, Sam started to bend to grab the keys, but Dean swiped them and had the key in the door before Sam could even move a foot.

"I got this man. Let's just get in and pack up."

The smell of char and smoke clung to the apartment like a disease. Officer Lance had said that most of the damage was contained to the bedroom. They had saved most everything. After some renovation, some other unlucky bastard could take this place.

Sam walked straight to the living room and dug though the bottom desk drawer until he found it: the ring box. Slowly opening the black velvet box, Sam found the silver ring with the modest diamond placed in the band that he had spent all of his savings on. Jess would have loved it.

Dean saw Sam pull out the black box; he could only assume what it was. He wasn't going to press his brother for information right now. If Sam had intended to marry that girl, it made a lot more since why this destroyed him so badly. As if he didn't have enough reason already.

Dean followed his younger brother around the room, helping him pack. Sam would pull the items; inspect them for a while, memories dancing before his eyes, while Dean put the boxes together. After Sam was done, he would hand the item off, where Dean would pack it.

It took a few hours, but slowly they made their way through the apartment. Four hours and 5 boxes later, they had only one room left: the bedroom.

Walking in was death. He felt the blood drip on his face, heard the shower running, and saw the love of his life, burning to death on the ceiling. Once again, he regretted the fact that he had ignored the visions.

It took Sam five minutes to process and walk all the way into their room. This was the last time he would be here. He didn't know if he wanted to rejoice at that fact or be depressed.

After packing up clothes, photo albums, books, picture frames and little kick knacks, Sam found himself with only Jess's bedside table left. He decided to clean it out bottom to top. Things at the bottom, Jessica didn't care as much about. The objects at the top, on the other hand, were most likely some of the last things she touched.

Dean decided to leave Sammy alone for a little bit, as he started moving the filled boxes to the car. They were almost wrapped up here and he figured his little brother could use some time alone with his thoughts.

Opening the top drawer Sam found some things he expected to find and two things he did not. The corners of Sam's mouth lifted at the sight of _Harry Potter and the Goblet of Fire_. The book was Sam and Jess's favorite of the series, and the one she would read in between books, when they weren't studying. Some nights Sam would stay up late reading the book to Jess, running his fingers through her hair as they cuddled up in bed. Those were the memories he would keep forever.

There were a few other random items he expected to find: remotes, letters from family, headphones, money and a half empty box of condoms. It was only two things that looked out of place, new to this drawer. In the back, right corner of the drawer, closest to the bed and out of sight, he noticed a notepad and brown paper bag.

Sam opened the bag and peered down into it, brows furrowed. Setting it beside him, he moved onto the notepad. The little pad was flipped to the third or four page. Apparently Jess had been trying to write something and kept changing her mind. It looked like she finally settled on something.

**_Dear Sam,_**

**_I'm nervous and I don't really know how to begin._**

**_I'm sorry I waited so long_**

**_I know this isn't a good time_**

**_I don't know if I'm going to make this a speech or a note. If it is a note I obviously have to rewrite this, now I'm rambling and talking to myself. Oh god, I hope you don't find this…_**

**_I have something, kind of big to tell you, and I really hope you don't freak out._**

Sam's heart was trying to break out of his ribcage. What was it Jess was so nervous about? They shared nearly everything. He flipped the page to continue reading.

**_So I have been wanting to tell you something for a while, but you had the LSAT and the interview and finals so it was always just a bad time._**

**_Please just think back to our talks about to future. You said, one day, you wanted to marry me, go to law school, and have children._**

**_Well we may be doing that in a different order. Please, Please, Please, don't freak out. But…. I'm pregnant. About two months now…_**

Sam flipped the page so fast that he thought he would rip it off. Time seemed to stand still and his heart appeared to stop. Jess was pregnant. The woman, he was madly in love with, and days away from proposing to, had been carrying his child. And he had left her home, alone, and she died. He hoped she would say she was kidding.

**_I know it's not the best time, that's why I waited. I wanted you to do that interview and tell you later so you wouldn't make you too distracted or anxious. I don't know._**

**_I don't expect you to be really happy about this or anything, I know with law school starting this is something totally unplanned and unwanted. But I can't fathom getting rid of our child. It has killed me to keep this a secret from you. I'm scared, but I'm so happy I could cry._**

He wouldn't have been mad. He would have dropped to his knees before her and vowed his life to her and their unborn child. He would have wrapped her in his arms and never let go. He would have worshiped her and promised to be everything his father wasn't, and more. He would have given them the world. But he couldn't now.

_**I'm scared now, and I'm sure when you first find out, it will be a little rocky, and you will be afraid. But I know who you are Sam, and I know that you will be an amazing father. I can't wait for the day we get to hold our little boy or girl in our arms.**_

_**I love you Sam. Know that, forever. From this day, until my last.**_

_**Love You Always,**_

_**Jessica**_

Tears streamed down Sam's face, tears he didn't know were falling until they crashed onto his arms. Laying the notepad down, he turned back to the bag. Dumping it out, he found a wrapped package, inside that a pregnancy test, inside of that a peed on stick with a little plus sign. He hadn't just loss Jess, he also lost a child. He failed his family, before he even knew he had one to fail.

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**A/N: **Reviews are very welcome! I'm going to put another one of these up soon. Feel free to send me your ideas!


	2. 2: The Price of Failure

**A/N: **Hey! Thanks for those of your reading! I really feel like a horrible person writing an idea this sad. Haha. I just couldn't get it out of my head. The next chapter won't be so depressing...it will be a little more upbeat. Thanks for reading!

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Rolling up the brown bag, he shoved it into the last box. Holding up the notepad Sam flipped it back to the first page; the note to him wasn't the only writing this contained. Doing a quick flip through the pages Sam saw there were what looked like names, numbers and other random notes. He didn't take the time to go through it; there would be time for that later. Right now he heard Dean walking back toward the room.

Wiping his face up quickly, trying to hide the evidence of his tears, he shoved the notepad in his pocket. Dean entered the room, clearing his throat to let Sammy know he was there. Sam picked up the box and headed for the door.

"You okay?"

"Fine. You don't need to worry. Let's go find the landlord and take off."

Dean could hear the raspy quality to Sam's voice; see the red rings around his eyes. He didn't want to ask any more questions if Sam didn't want to answer.

A few hours later, they had dealt with the landlord and took off for Bobby's house. Sam said he would take the first six-hour driving shift and let Dean get some sleep. Dean passed out pretty quick. Sam, seeing his brother fast asleep, finally decided to let a few tears fall as he gave over to thoughts of what could have been. This was dangerous, the whole what if game, but Sam couldn't stop.

The hours passed faster than he thought possible, he was in such a daze. Dean took over when they pulled over at a rest stop for a few minutes. After grabbing some drinks and snacks from the vending machines they hit the road again. It wasn't long until Sam was immersed back into his nightmares.

Dean could see Sammy fidgeting and hear the small noises that escaped his lips. He didn't know if he should wake him or not. Probably best to just let him keep sleeping.

It had been twelve hours on the road and they were somewhere in Wyoming, halfway to Sioux Falls, South Dakota. Dean pulled over at a motel and let Sam check them in as he grabbed some grub for the two at the local diner. There hadn't been much talking and Dean figured there wasn't going to be.

The boys ate in silence, and after ten minutes of picking at his food Sam took a shower and climbed into bed. The next morning after breakfast and checkout the boys followed the same routine as the day before. Sam drove first and then Dean afterwards.

Things start to mess with your sight after nearly twelve hours of staring at moving surroundings. They were 45 minutes from Bobby's when Sam finally had to close his eyes to get a break from window watching. When he opened his eyes back up, he swore he saw Jess.

They were slowly moving though some tiny town when Sam saw her. In shock he moved closer to the window attempting to get a better look. She was watching him pass, standing there, beautiful as always, with her blond curls flowing free, and a white dress on.

The weird part was, besides her obviously being dead, was that though the car was moving she appeared to stay right in Sam's view. Sam could see the small smile form on her lips, and then she opened her mouth, it looked like she uttered his name.

He had to know what she would say. He tried to yell for her, but he couldn't get the words out. Slowly she lifted her arms, turned to the side and placed her hands on her stomach. Pushing the free flowing material of the dress down, right hand on the top of her belly and left on the bottom, to reveal a hardly noticeable bump.

She was showing him that she was pregnant. She was showing him what was just out of his reach: her and their child. Clawing for the handle of the door Sam tried to get out of the car and run to her, except there was no handle. Sam's eyes turned back to Jess, pleading with her to help him follow her. Once again her mouth opened, but these words he heard:

"Why did you fail us? I thought you loved me more that life itself."

Gasping for air Sam awoke from his nightmare of a nap he had fallen into. They were parked in front of Bobby's, and Dean was just taking the keys out of the ignition. Jumping out of the car, Sam took off. He saw Dean's worried gaze and Bobby heading out to greet them.

Dean watched his brother take off around the beat up wooden barn that he parked out front of. He pretended he didn't hear Sam puke and gasp for air. Hurrying to the back of the car, he opened the trunk, removed his duffel, and took off to meet Bobby. The least he could do was save Sam the embarrassment of Bobby hearing.

"Hey, Bobby! Thanks for letting us crash here for a bit."

"You know you boys are always welcome."

Bobby looked around behind Dean, confused as to why Sam hadn't come out yet. Before he could make his way around Dean to try to find the younger Winchester, Dean grabbed his shoulder and turned him toward the house.

"Why don't you just show me where we will be sleeping? The past few days have been pretty hard on Sam, I think he needs a moment."

"Well… alright."

Sam finally meandered into the house, carrying his bag, nearly a half hour later. Bobby intercepted him in the kitchen.

"Hey son. It's good to see ya."

Bobby patted the boy on the back. Sam answered in a rough voice.

"You too Bobby, thanks for having us. Where should I put this?"

He lifted his shoulder to show he was talking about his bag. Bobby pointed back behind him in the general direction of the stairs.

"Upstairs, first door on your left. The room you usually take. I haven't touched it since you boys were last here."

"Thanks, again…"

"No problem. You just come on down when you're done putting your things up and catch up with me, would ya."

Sam trudged up the stairs and to his old bedroom. This had been the room he had stayed in on and off since he was a child. They had spent a good portion of their life here, and still came when they needed a place to crash or work on a new case. Bobby was more of a father to them than their dad ever had been.

Once in the room he unpacked and went to the bathroom to wash his mouth out and brush his teeth. Upon returning to the room he realized he had no desire to go downstairs and have to make small talk, or avoid things that made him think of Jessica.

Sitting down on the edge of the bed Sam decided to pull the notepad out of his pocket. He read the note about ten more times before he finally had enough of the torture and flipped it shut. When he did this, he once again noticed the names on the front page.

Now studying the words more closely, he saw a title on the page: baby names. Doing a quick scan of the list before his brain could register the pain. He saw his name, under boys, with a heart drawn beside it. Things kept getting too real for him; he couldn't take this.

Dean was downstairs filling Bobby in on everything that had been going on. He told him what leads they had on their dad, and on the demon that had killed Jess and their mom. If anyone could help if would be Bobby. He was pretty much the go to and connected to everyone in the hunter world.

Wondering what was taking Sammy so long to come down, Dean decided to go check on his little brother. He was getting a lot more worried about him of late. Taking the steps two at a time, he reached his brothers room in a few seconds, and pushed the door open after one quick sharp knock on the doorframe.

Sam heard the knock, but before he could say go away, his big brother entered. He should have closed his door, and locked it. Stunned he stood up and turned away trying to clear his face.

Dean strode over to his brother. He couldn't stand to see him in pain. Grabbing Sam roughly by his upper arm he spun him around and embraced him. He was going to try to give Sammy any kind of comfort he could.

"Hey! We are going to get that son of a bitch! I swear to you. I know you are hurting and don't want anyone to know, but I am here for you Sammy."

Pain throbbed through Sam's chest and his throat tightened as he attempted to hold back his tears. A sob broke though and he lost it in his brother's arms. Tears welled in Dean's emerald eyes as he felt the sob rake though Sammy's body.

"I failed her Dean. I failed Jess."

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**A/N: **Thanks for reading! Please feel free to review or give ideas. The next chapter is going to be a bit different from the last two!

P.S. : to those of you with finals...like me...I understand and keep up the hard work! Good luck! Don't be like me and avoid studying by writing! :)


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